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Determination of the absolute configuration of sulfinyl glycosides: the role of the exo-anomeric effect

✍ Scribed by Noureddine Khiar

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
112 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

The diastereoselective synthesis and conformational study of aand b-ethylsulfinylglycosides have been studied. It was found that while b-(S S )-sulfinyl glycosides are flexible b-(R S )-sulfinyl glycosides exists in a major conformation stabilized by the exo-anomeric effect. The generality of the hyperconjugative delocalisation gives rise to a general rule for the determination of the absolute configuration of sulfinyl glycosides by 1 H or 13 C NMR spectroscopy without need of chemical shift reagents.

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## Resolution of pentahelicene (4) was recently described['! We have now succeeded in the first allocation of absolute configuration to a helicene, namely to (+ )-( 4). The fundamental investigations of Mislow et al. ['], later confirmed by X-ray structure analysis[31, have shown that